So a realtor is a big gamble at that point. 

But I'm still fairly new to MTR/STR so I'm learning as I go.

Gambling addiction,drug addiction, seems familiar.

I'll then list my properties on the high end of whatever I think fair market rent is.

How is this fair to the broker?))

Per fair housing regulations, I can't answer this question. 

A straightforward response like, 'Thanks for your interest, but we’ll need confirmation that the buyer can cover the full (or close to full) listing amount,' seems fair.

Is it fair?

I would only hire out for major work I can't do myself or emergency repairs.I've dealt with older houses before and the house may be fine for occupants but there's still usually lots of things that can be fixed / improved so it seems a house that isn't perfect would give more opportunities for ongoing maintenance of this sort.To me it seems fairly straightforward to meet the time requirements but I think I need to have extensive documentation?

Some fair criticism for sure.